Here’s what it actually felt like to have my team.
We were not a traditional company. We had a Regus office in The Woodlands, Texas, one room, enough for a handful of people. Most of the team was spread across the country: Virginia, Florida, Utah, Pennsylvania, more. I was on the road over 150 days a year, hitting customers in New York, Los Angeles, everywhere in between. We worked remote before remote was popular.
When we landed on-site together, we skipped the hotels and got an Airbnb. Everyone had their own room, but by the end of the night we’d all end up in the same kitchen or on the same porch, drinking and smoking and talking shit and laughing. That’s what the team was: people you worked hard with, played hard with, and actually liked. Most of them came from previous jobs, people I’d already trusted with real work. My architect had been with me practically from the beginning, my back office person was in Texas keeping the whole thing running, and my SCCM expert 🙌, I’d known him for fifteen years.
I was the sales engine: keeping the customers, making the calls, flying out to maintain the relationships. The operations and delivery ran independently, the hundred small fires got put out before they reached me, and that was the point. But I was the one generating the revenue, and when we started building our own inbound pipeline, I became the one running marketing too.
And then there was Brittany.
Brittany is my sister-in-law, and she was my assistant, which meant she was everywhere I was. She booked my travel and sat with me all day, every day. And it wasn’t just work: Brittany and Jon were at our house, we were out at dinner, and when we weren’t working we were still together. The line between team and family was blurry by design.
What she actually did is hard to describe. I have a brain that runs fast and loud and in all directions at once. I could sit across from her and just start going: the deal I was thinking about, the customer issue I hadn’t resolved, the half-formed idea I’d been turning over since 3am, all of it pouring out in whatever order it came. She would listen to the whole mess. And then she’d start asking questions. “What about this? Did you remember that? What does that mean for the other thing?” Not because she understood every technical detail, she got there eventually, but that wasn’t the point. The point was the listening and the questions. The process forced me to untangle it. By the time we were done, I knew what I actually thought and what I had to do.
She tracked everything, kept notes, kept me focused, and knew where every thread was at any given moment. She was my confidant. And I’ll tell you something: even now, laying this out, I’m completely underselling what she actually did.
COVID hit in March 2020. We were nine months into a transition, trying to build our own inbound pipeline instead of relying on referrals and relationships. We’d hired a HubSpot partner. We were spending $20,000 a month learning how to do marketing in real time. The committed pipeline we were counting on to carry us through the transition evaporated.
The math stopped working. I made the tough call.
Closing Identity Solutions wasn’t a pivot. It wasn’t a strategic restructuring. It was a decision I made in a week that took years to process. The money piece is the easy part to explain; the other part is harder.
I had people working for me who were my closest friends. People who trusted me with their livelihoods, who had built careers inside what we’d built. Some of them understood. They saw the numbers, they knew the market, they were gracious about it. Some of them were pissed off and haven’t spoken to me since. If I had to do it over again, I’d do a lot of things differently. All of that is true. All of it belongs in this story.
The embarrassment was real, and it lasted a long time. These were my people. I felt like I’d failed every one of them, and for a long time I couldn’t separate that feeling from who I was.
Then we moved countries.
We made the decision on July 4th. We landed in Sweden on August 15th.
We were living in California when COVID hit and everything was closed. You couldn’t go anywhere, couldn’t do anything, and we were spending a lot of money to live in a place where none of the things that made it worth it were available. Then the landlord wanted to raise the rent in the middle of a global pandemic and we felt we needed a change.
So we started looking at options and at some point, Sweden came up. My wife is Swedish. Our children needed to live there at some point while they were still kids or their citizenship could be in jeopardy. Moving back to Texas would have cost roughly the same as moving to Sweden. So we ordered a container, threw everything in it, bought tickets, and went. LAX looked like a ghost town. We had no plan beyond the flight so we got an Airbnb and found a place in Sigtuna during that first month.
Six weeks between the decision and landing. That’s how we moved countries.
We stayed in Sigtuna for two and a half years in a beautiful house on a lake. Then reality caught up and we moved closer to family. We ended up in a 115-square-meter house that was too small, too old, in the middle of nowhere. Laguna Beach to rural Sweden.
When you move countries as an adult, you lose something people don’t talk about. You lose your competence. In the US, I could read a contract and know what to look for. I knew how credit worked, how insurance worked, who to call when something broke. All of that life experience, decades of it, doesn’t transfer. I had money in the bank and I couldn’t get a cell phone plan because I couldn’t prove Swedish income. I offered to pay for a full year up front. Didn’t matter. My retired mother-in-law had to co-sign because she had a Swedish credit history and I didn’t.
Everything familiar is gone at once and you have to rebuild it from scratch, in a language you don’t speak, in a culture that runs on different rules. I spent the better part of a year trying to figure out cornbread. Their cornmeal is too fine, so you have to use polenta. They don’t have buttermilk, they have something called filmjölk that’s too fatty, so you use the light version. No self-rising flour, so you make it yourself. The baking powder works differently here, so the ratios are always off. That’s one thing. One recipe.
Eventually I went back to work as an employee. You go from moving the pieces to being one, and spend the rest of your time doing the stuff that used to just get done.
And I want to make one thing clear: I love living here and I have zero desire to move back. But I wasn’t ready for how much of my identity was tied to a life that no longer existed while sitting at a job that wasn’t using me to the fullest, and for the only time in my life I started to doubt myself.
I knew what I had when I had it. When I closed the company, I knew what I was losing. Not just the team, not just the revenue but the ability to dump everything in my head, have someone help me find the thread, and the capacity to do something greater than the sum of our parts. I pushed it down, kept my nose to the grindstone, and learned how to function without it.
“That’s in the past, we are here now, stop being a baby, move on.”
And I believed it for a while.
Then I found AI.
I could dump the mess in my head and have something help me untangle it. I could think out loud again and get something useful back. I could have an idea and actually build it. The orchestra was starting to crescendo and it wasn’t me playing. The gap I’d been carrying around for years started closing, and I got excited about technology in a way I hadn’t felt in a long time.
It wasn’t until that happened that I realized I hadn’t gotten over it at all. I’d just gotten used to operating without it.
I’m not trying to convince anyone that I have it all figured out. I don’t. But I’m getting a lot better at what not to do.
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